Town

    Where to Stay in Pittsfield

    Pittsfield is the largest city in the Berkshires, and North Street has restaurants, bars and theaters that serve residents as well as visitors. Barrington Stage Company and the Colonial Theatre, part of the Berkshire Theatre Group, both perform here, and the First Fridays Artswalk brings out the city's galleries. Herman Melville wrote Moby-Dick at Arrowhead, his farm on the southern edge of town, which is open for tours from May through October. Canoe Meadows, a Mass Audubon reserve, has easy walks along the Housatonic River inside the city, and Jiminy Peak is about 12 miles north in Hancock. Pittsfield suits travelers who want a city base with grocery stores, restaurants and a walkable downtown, and it usually costs less than Lenox or Stockbridge.

    Hotel on North

    Hotel on North

    Pittsfield · Hotel

    A hotel in a converted 19th-century building on North Street in Pittsfield, the largest city in the Berkshires. There is an art gallery on the ground floor and a restaurant. Barrington Stage Company and the Colonial Theatre are nearby, and the location sits midway between north and south Berkshire County.

    Design-forwardWalkableHistoric
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    Why Stay in Pittsfield

    • •Barrington Stage Company and the Colonial Theatre give Pittsfield performances well beyond the summer season.
    • •Herman Melville's Arrowhead, where he wrote Moby-Dick with a view of Mount Greylock from his study, is open for tours from May through October.
    • •Jiminy Peak, about 12 miles north, has 45 trails and night skiing.

    What Makes This Area Interesting

    • •Arrowhead: Herman Melville's farmhouse on Holmes Road; open for tours May through October, including the study with its view of Greylock.
    • •Canoe Meadows: a Mass Audubon reserve with easy trails along the Housatonic River; good birding during spring migration.
    • •Berkshire Museum: downtown Pittsfield; natural history and fine art collection; the aquarium is good for families.
    • •Jiminy Peak Mountain Resort: about 12 miles north in Hancock; 45 ski trails, night skiing, and a mountain coaster and zip lines in summer.

    Explore Nearby Towns

    LenoxNorth AdamsWest Stockbridge
    Boutique Hotels in the BerkshiresHistoric Inns of the Berkshires

    Frequently Asked

    Year-round — more so than most Berkshires towns. The theater calendar runs through winter; Jiminy Peak makes the ski season viable; the arts scene runs regardless of Tanglewood. Summer is still the peak for visitors using Pittsfield as a base for the broader region.

    About 2.5 to 3 hours from the George Washington Bridge via the Taconic Parkway and Route 20. From Boston, roughly 2.5 hours via I-90 (the Mass Pike) to Exit 10 (Lee), then north on Routes 20 and 7.

    Pittsfield has more urban infrastructure and lower prices. Lenox has the inn experience and direct proximity to Tanglewood. If the goal is a town that functions year-round with restaurants, theaters, and services, Pittsfield works better. If the goal is Tanglewood weekends and the inn-stay experience, Lenox is more central.
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